ES2239226T3 - Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos. - Google Patents

Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos.

Info

Publication number: ES2239226T3
Authority: ES; Spain
Prior art keywords: indole; oxazolo; formula; compounds; cycloalkyl
Prior art date: 2001-04-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES02727527T

Other languages

English (en)

Spanish (es)

Inventor

Kai Schiemann

Henning Bottcher

Joachim Leibrock

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-04-30

Filing date

2002-04-05

Publication date

2005-09-16

2002-04-05 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

2005-09-16 Application granted granted Critical

2005-09-16 Publication of ES2239226T3 publication Critical patent/ES2239226T3/es

2022-04-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003446 ligand Substances 0.000 title claims description 16
230000000862 serotonergic effect Effects 0.000 title claims description 10
CIACKZWMHRQXBR-UHFFFAOYSA-N 6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical class N1C=CC2=C1C=CC1=C2N=CO1 CIACKZWMHRQXBR-UHFFFAOYSA-N 0.000 title description 6
150000003839 salts Chemical class 0.000 claims abstract description 82
150000001875 compounds Chemical class 0.000 claims abstract description 61
239000012453 solvate Substances 0.000 claims abstract description 25
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
125000004429 atom Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
239000004305 biphenyl Substances 0.000 claims abstract description 5
235000010290 biphenyl Nutrition 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
-1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims description 154
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 13
229940079593 drug Drugs 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
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206010012289 Dementia Diseases 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 6
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
230000006872 improvement Effects 0.000 claims description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
SPFWHUJSJQVRMB-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCN1CCC(O1)=NC2=C1C=CC1=C2C=CN1 SPFWHUJSJQVRMB-UHFFFAOYSA-N 0.000 claims description 3
AJRVPWOPYOKQDN-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(2-imidazol-1-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CCN1C=CN=C1 AJRVPWOPYOKQDN-UHFFFAOYSA-N 0.000 claims description 3
FBERXFHTIIVDCZ-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 FBERXFHTIIVDCZ-UHFFFAOYSA-N 0.000 claims description 3
ZNJKKGYLILLJRG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(5-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC3=CNC4=CC=C(C=C43)OC)=C1C=C2 ZNJKKGYLILLJRG-UHFFFAOYSA-N 0.000 claims description 3
CHGLCUWMBUYUCI-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound O1C(CCC)=NC(C2=3)=C1C=CC=3NC=C2C1CCN(C)CC1 CHGLCUWMBUYUCI-UHFFFAOYSA-N 0.000 claims description 3
PXYFHCRZTJGCCR-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 PXYFHCRZTJGCCR-UHFFFAOYSA-N 0.000 claims description 3
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239000007800 oxidant agent Substances 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
231100000167 toxic agent Toxicity 0.000 claims description 3
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125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims description 2
231100000867 compulsive behavior Toxicity 0.000 claims description 2
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
101100134922 Gallus gallus COR5 gene Proteins 0.000 abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 110
239000000243 solution Substances 0.000 description 61
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QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
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208000035475 disorder Diseases 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 7
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150000003254 radicals Chemical class 0.000 description 7
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229940076279 serotonin Drugs 0.000 description 6
239000000126 substance Substances 0.000 description 6
VOCGEKMEZOPDFP-UHFFFAOYSA-N 2-(6-methoxy-1h-indol-3-yl)ethanamine Chemical compound COC1=CC=C2C(CCN)=CNC2=C1 VOCGEKMEZOPDFP-UHFFFAOYSA-N 0.000 description 5
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HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 4
RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 4
KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 4
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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229960003638 dopamine Drugs 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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150000003462 sulfoxides Chemical class 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
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- A61P25/16—Anti-Parkinson drugs
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
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Chemical Kinetics & Catalysis (AREA)
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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
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Psychology (AREA)
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Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Obesity (AREA)
Child & Adolescent Psychology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Nutrition Science (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

ES02727527T 2001-04-30 2002-04-05 Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos. Expired - Lifetime ES2239226T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10121217		2001-04-30
DE10121217A DE10121217A1 (de)	2001-04-30	2001-04-30	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden

Publications (1)

Publication Number	Publication Date
ES2239226T3 true ES2239226T3 (es)	2005-09-16

Family

ID=7683302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES02727527T Expired - Lifetime ES2239226T3 (es)	2001-04-30	2002-04-05	Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos.

Country Status (13)

Country	Link
US (2)	US7291633B2 (de)
EP (1)	EP1392699B1 (de)
JP (1)	JP4485746B2 (de)
AR (1)	AR033267A1 (de)
AT (1)	ATE291026T1 (de)
AU (1)	AU2002257752B2 (de)
CA (1)	CA2445835C (de)
CZ (1)	CZ20033194A3 (de)
DE (2)	DE10121217A1 (de)
ES (1)	ES2239226T3 (de)
HU (1)	HUP0304034A2 (de)
SK (1)	SK14482003A3 (de)
WO (1)	WO2002088139A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10121217A1 (de) *	2001-04-30	2002-10-31	Merck Patent Gmbh	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden
AU2003227522A1 (en) *	2002-05-30	2003-12-19	Neurosearch A/S	3-substituted quinuclidines and their use
WO2005041957A1 (en) *	2003-10-29	2005-05-12	Pfizer Products Inc.	Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors
WO2007031846A2 (en) *	2005-09-14	2007-03-22	University Of The Witwatersrand, Johannesburg	Pharmaceutical composition
DK2909204T3 (en)	2012-10-12	2019-04-01	Broad Inst Inc	GSK3 INHIBITORS AND METHODS FOR USE THEREOF
CA2913108A1 (en) *	2013-05-24	2014-11-27	Nestec S.A.	Pathway specific assays for predicting irritable bowel syndrome diagnosis
KR20190136063A (ko) *	2017-04-05	2019-12-09	더 브로드 인스티튜트, 인코퍼레이티드	글리코겐 신타제 키나제 3 (gsk3) 억제제로서의 트리시클릭 화합물 및 그의 용도

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE178893T1 (de)	1990-01-11	1999-04-15	Upjohn Co	6,7,8,9-tetrahydro-3h-benz(e)indolheterocyclen mit wirkung auf das zentrale nervensystem
TW263508B (de)	1991-02-12	1995-11-21	Pfizer
CA2194984C (en) *	1994-07-26	2002-07-02	John Eugene Macor	4-indole derivatives as serotonin agonists and antagonists
JPH11513391A (ja) *	1995-10-03	1999-11-16	ザスクリップスリサーチインスティテュート	Ｃｃ−１０６５及びズオカーマイシンのｃｂｉ類縁体
DE69908330T2 (de) *	1998-03-09	2004-02-12	H. Lundbeck A/S	5-heteroaryl-substituierte indole
DE10045112A1 (de) *	2000-09-11	2002-03-21	Merck Patent Gmbh	Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems
DE10121217A1 (de) *	2001-04-30	2002-10-31	Merck Patent Gmbh	6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden

2001
- 2001-04-30 DE DE10121217A patent/DE10121217A1/de not_active Withdrawn
2002
- 2002-04-05 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-05 EP EP02727527A patent/EP1392699B1/de not_active Expired - Lifetime
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 2002-04-05 AT AT02727527T patent/ATE291026T1/de not_active IP Right Cessation
- 2002-04-05 ES ES02727527T patent/ES2239226T3/es not_active Expired - Lifetime
- 2002-04-05 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu unknown
- 2002-04-26 AR ARP020101530A patent/AR033267A1/es not_active Application Discontinuation
2007
- 2007-10-30 US US11/928,961 patent/US7741343B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20080051394A1 (en)	2008-02-28
DE10121217A1 (de)	2002-10-31
JP2004527562A (ja)	2004-09-09
AR033267A1 (es)	2003-12-10
SK14482003A3 (sk)	2004-03-02
DE60203283T2 (de)	2006-03-30
ATE291026T1 (de)	2005-04-15
DE60203283D1 (de)	2005-04-21
US20050101649A1 (en)	2005-05-12
EP1392699B1 (de)	2005-03-16
US7291633B2 (en)	2007-11-06
EP1392699A1 (de)	2004-03-03
AU2002257752B2 (en)	2008-02-28
WO2002088139A1 (en)	2002-11-07
JP4485746B2 (ja)	2010-06-23
CZ20033194A3 (cs)	2004-02-18
CA2445835A1 (en)	2002-11-07
HUP0304034A2 (hu)	2004-04-28
CA2445835C (en)	2012-01-03
US7741343B2 (en)	2010-06-22

Publication	Publication Date	Title
HU211566A9 (en)	1995-12-28	New benzimidazoline-2-oxo-1-carboxylic acid derivatives useful as 5-ht receptor antagonists
JP2025533411A (ja)	2025-10-07	Ｋｉｆ１８ａ阻害剤化合物、医薬組成物並びにその製造方法及び応用
MX2008015329A (es)	2008-12-12	Derivados 1-sulfonilindazolilamina y -amida como ligandos de 5-hidroxitriptamina-6.
US7741343B2 (en)	2010-06-22	6H-oxazolo[4,5 e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
AU700561B2 (en)	1999-01-07	Agent for potentiating nerve growth factor activity containing 1,2-ethanediol derivative or salt thereof
JP4593879B2 (ja)	2010-12-08	ニコチン性アセチルコリンレセプターリガンドおよび／またはセロトニン作動性リガンドとしてのジヒドロイミダゾ［４，５−ｅ］インドールおよび７Ｈ−ピロロ［３，２−ｆ］キノキサリン誘導体
EP3820867B1 (de)	2023-09-13	Verbindungen und zusammensetzungen zur behandlung von mukoviszidose
AU2002310904A1 (en)	2003-04-17	Dihydroimidazo[4,5-e]indole and 7H-pyrrolo[3,2-f]quinoxaline derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
AU2002257752A1 (en)	2003-04-17	6H-OXAZOLO[4,5-E]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands
NZ194245A (en)	1984-07-06	4-phenyl-4,5,6,7-tetrahydropyrrolo(2,3-c)pyridines
JP2004527534A (ja)	2004-09-09	ニコチン性アセチルコリン受容体リガンド
GB2225574A (en)	1990-06-06	Aryl ureas and carbamates as 5-htä antagonists
JP2006503859A (ja)	2006-02-02	受容体拮抗薬としてのアザ二環式スピロエーテル誘導体
KR20010112231A (ko)	2001-12-20	５―ｈｔ 재흡수 저해제 및 ５―ｈｔ１ｂ／１ｄ리간드로서의 아미드 및 우레아 유도체